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Ben Affleck Says 13-Year-Old Son Asked for $100 to Bet on Sports

He used a Jimmy Kimmel appearance to frame a parenting lesson rooted in his family's gambling past.

Harris Recounts Hearing Trump Sell His Book During Post‑Attempt Call on Kimmel

Nick Reiner Booked in Suspected Killing of Parents Rob and Michele Reiner in Los Angeles

Miley Cyrus Confirms Engagement to Musician Maxx Morando After Surprise Proposal

Kate Winslet Recalls Near Wardrobe Mishap During First Meeting With King Charles

Samuel L. Jackson Jokes on Kimmel That Lamar Jackson Is His 'Bastard Son'

Riyadh Comedy Festival Ends as Human Rights Watch Rejects Donations From Aziz Ansari and Other Performers

Jeff Bridges Revives 'The Dude' on Kimmel to Denounce ICE Raids

Julia Louis-Dreyfus Reveals Her Father Was on Nixon’s ‘Enemies List’ on Kimmel’s Reinstated Show

Denzel Washington Says His Name Is Properly Pronounced ‘DEN‑zuhl’ on Jimmy Kimmel Live

Brooks Nader Dodges Jannik Sinner Dating Question on Jimmy Kimmel Live

Bono Backs Springsteen, Denies Trump’s Payment Claims

Nathan Fielder Slams FAA Over Pilot Communication Training

Miley Cyrus Recounts ICU Stay After Hollywood Walk of Fame Video Shoot